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Rich Hill is scheduled to start vs. the Cubs on Tuesday night, more than 20 years after making his MLB debut at Wrigley Field

July 22, 2025 by WGN 9

Rich Hill once took the mound at Wrigley Field for his MLB debut.

That was a long time ago.

He’ll ascend that same mound again a little more than 20 years later on Tuesday night, and it’s not to throw out a ceremonial first pitch.

No, Hill is still an active big-leaguer, and he’s the scheduled starter for the Kansas City Royals for the second game of their three-game series against the Cubs at Wrigley Field this week.

Hill, now 45 years old, was called up from Triple-A Omaha to make the start Tuesday. Assuming he pitches as scheduled, the long-tenured left-hander will throw a pitch for his 14th different MLB team when he delivers to the Cubs in the bottom of the first inning.

And he’ll throw it against the team he began his long big-league career with.

Drafted 3 times

Hill was first drafted in the last millennium, in the 36th round of the 1999 MLB June Amateur Draft out of Milton High School in Massachusetts. Being such a late-round pick, Hill did not sign a pro contract and instead went to play in college at the University of Michigan.


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His draft stock improved considerably, and he was drafted again, this time by the Anaheim Angels in 2001. But Hill again chose not to sign and continued his career at Michigan.

He was drafted for a third time, by the Cubs in the fourth round in 2002. This time Hill signed, beginning a pro career that’s still going almost a quarter-century later.

Cubs career

Three years after being drafted by the Cubs, Hill made his MLB debut at Wrigley Field, on June 15, 2005, against the Florida (now Miami) Marlins in a relief role.

Some of the names from the lineups that day give perspective as to how long Hill’s been around.

The starting pitcher for the Cubs was Greg Maddux. The Cubs’ starting outfield, left to right, was Todd Hollandsworth, Corey Patterson and Jeromy Burnitz. The batters that Hill faced in his first MLB inning were Luis Castillo, Miguel Cabrera, Carlos Delgado, Mike Lowell, Paul Lo Duca and Juan Encarnación.

Hill gave up three hits and two runs in that inning, but he also recorded the first two of his 1,428 career strikeouts, going into Tuesday night’s game.

Hill became a member of the Cubs’ starting rotation after that debut, and his best season came in 2007, when he made 32 starts for a team that won 85 games and the NL Central title under Lou Piniella. Hill went 11-8 with a 3.92 ERA over a career-high 195 innings.

Long journey

Following the 2009 season, Hill signed in free agency with the Baltimore Orioles, the first of many times his name has appeared on the MLB transactions wire.

Hill’s journey has included four separate stops with the Boston Red Sox, including one appearance last season, as well as one stop each with the Cubs, Orioles, Cleveland then-Indians, Los Angeles Angels, New York Yankees, then-Oakland A’s, Los Angeles Dodgers, Minnesota Twins, Tampa Bay Rays, New York Mets, Pittsburgh Pirates, San Diego Padres and now the Royals, assuming he starts Tuesday.


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Hill’s most lengthy and successful tenure came with the Dodgers during four straight seasons from 2016-19, the team he’s pitched the most total innings for. He made two starts, in fact, for the Dodgers against the Cubs in NLCS games.

Hill twirled six shutout innings in Game 3 of the 2016 NLCS, outdueling Jake Arrieta in a game the Dodgers won, 6-0, to take a 2-1 series lead. It was, of course, the last game the Cubs would lose in that series on their way to a World Series title.

But Hill and the Dodgers got revenge a year later. Hill started Game 2 of the 2017 NLCS and allowed just a run in five innings. He left with a no-decision, but the Dodgers would win on a walk-off homer in the bottom of the ninth on their way to beating the Cubs in five games.

The man who hit that walk-off homer? It was Justin Turner, who now plays for the Cubs and could possibly face Hill on Tuesday night.

Filed Under: Cubs

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